Tryptamine

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Tryptamine
Tryptamine structure.svg
Tryptamine-3d-sticks.png
Names
IUPAC name
2-(1H-Indol-3-yl)ethanamine
Identifiers
61-54-1 YesY
ChEMBL ChEMBL6640 N
125
Jmol 3D model Interactive image
PubChem 1150
  • InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
    Key: APJYDQYYACXCRM-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C(=CN2)CCN
Properties
C10H12N2
Molar mass 160.22 g·mol−1
Appearance white to orange crystalline powder[1]
Melting point 113-116˚C[1]
Boiling point 137˚C (0.15 mmHg) [1]
negligible solubility in water[1]
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Tryptamine is a monoamine alkaloid. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which the name derives. Tryptamine is found in trace amounts in the brains of mammals and is hypothesized to play a role as a neuromodulator or neurotransmitter.[2]

Tryptamine is the common functional group in a set of compounds termed collectively substituted tryptamines. This set includes many biologically active compounds, including neurotransmitters and psychedelic drugs.

The concentration of tryptamine in rat brains is about 3.5 pmol/g.[3]

Plants containing tryptamine

Many plants contain small amounts of tryptamine. It is a feedstock for the metabolic pathways which influence plant growth and microbiome. For example, it is found as a possible intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid.[4] Higher concentrations can be found in many Acacia species.

Role in vertebrates

Tryptamine acts as a non-selective serotonin receptor agonist and serotonin-norepinephrine-dopamine releasing agent (SNDRA), with a preference for evoking serotonin and dopamine release over norepinephrine release.[5][6][7] It is rapidly metabolized by MAO-A and MAO-B,[8] and for this reason, has a very short in vivo half-life.

Tryptamine is documented as a noncompetitive inhibitor of serotonin N-acetyltransferase (SNAT) in mosquitoes.[9] SNAT catalyzes the anabolic metabolism of serotonin into N-acetylserotonin, another neuromodulator and the immediate precursor for melatonin.

Synthesis

The Abramovitch–Shapiro tryptamine synthesis is an organic reaction for the synthesis of tryptamine.[10]

General structure of substituted tryptamines

See also

References

  1. 1.0 1.1 1.2 1.3 http://www.chemicalbook.com/ProductChemicalPropertiesCB8192006_EN.htm[full citation needed]
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External links